This invention relates to novel 1-dimethylcarbamoyl-3-substituted-5-substituted-1H-1,2,4-triazoles which are useful as insecticides, acaricides, molluscicides and/or plant growth regulating agents, compositions containing those compounds and methods of use.
The search for compounds which have a combination of excellent activity and low undesirable toxicity is a continuing one because of factors such as the desire for compounds exhibiting greater activity, better selectivity, low undesirable environmental impact, low production cost and effectiveness against insects resistant to many known insecticides.
Certain compounds of the present invention, as defined herein, are particularly suitable for controlling plant-destructive insects from the order Homoptera in agriculture and horticulture. Certain compounds of the present invention, as defined herein, control foliage feeding insects in other orders such as Coleoptera, Lepidoptera and/or acarids as shown by the biological evaluation data herein. Certain compounds of the present invention as more fully defined herein are particuarly suitable for use in regulating plant growth. Further, certain compounds of the present invention as more fully defined herein are particularly suitable for controlling molluscs.
Certain 1,2,4-triazoles have been disclosed as having pesticidal activity. U.S. Pat. No. 3,308,131 describes a group of 1,2,4-triazoles having the general formula ##STR1## where X is oxygen or sulfur, R.sup.5 and R.sup.6 are aliphatic groups containing up to 14 carbons and which may be joined to form a heterocyclic ring with the carbamoyl nitrogen atom and R.sup.7 and R.sup.8 which together contain up to 14 carbon atoms, are free from aliphatic unsaturation and are selected from hydrogen, halogen, sulfonyl, mercapto, cyano, hydrocarbyl, halohydrocarbyl, nitrohydrocarbyl, hydroxycarbyloxycarbonylhydrocarbyl, hydrocarbylsulfonyl, hydrocarbylmercapto, nitrohydrocarbylmercapto, halohydrocarbylmercapto, aminohydrocarbylmercapto and hydrocarbyloxyhydrocarbyl. These compounds are said to be useful as insecticides, in dyeing textiles and as analgesics.
U.S. Pat. No. 4,291,043 describes 1-N,N-dimethyl-carbamoyl-3(5)-alkyl-5(3 )-alkylthioalkylthio-1,2,4-triazoles having insecticidal activity. The 3(5) substituents include i-propyl, s-butyl, t-butyl or optionally methyl-substituted cyclopropyl and a group having the formula EQU --S--CH(R')--(CH.sub.2).sub.n --S--R"
where R' is H or methyl, R" is lower (C.sub.1 -C.sub.4)alkyl and n is zero or 1.
U.S. Pat. No. 3,973,028 describes 1-dimethyl-carbamoyl-3-branched alkyl-1,2,4-triazol-5-yl-(N-substituted)sulfonamides having insecticidal activity.
U.S. Pat. No. 4,054,664 describes 1(2)-(N,N-disubstituted carbamoyl)-3,5-substituted-1,2,4-triazoles having insecticidal activity. The 3(5) substituents include isopropyl, s-butyl, t-butyl, and S--R where R is methyl, ethyl, propyl, vinyl, prop-2-ynyl, but-2-enyl or 2-haloalkyl.
U.S. Pat. No. 4,160,839 discloses 1-N,N-dimethylcarbamoyl-3,5-substituted-1,2,4-triazoles having insecticidal activity. The 3-substituents include t-butyl, propyl, cyclopropyl, isopropyl or 1-methylpropyl. The 5-substituents include S--R where R is 2-propynyl, allyl, 2-bromoallyl, 2-chloroallyl, 2-methylallyl, 1-methylallyl or 2,3,3-trichloroallyl.
U.S. Pat. No. 4,220,790 discloses 1-N,N-dimethyl-carbamoyl-3-tert-butyl-5-methylthio-1,2,4-triazole having insecticidal activity.
European Patent Application 0029407 discloses 1-N,N-dimethylcarbamoyl-3(5) -alkyl-5(3) -alkoxyalkylthio-1,2,4-triazoles where the 3(5)-substituent is isopropyl, sec-butyl, t-butyl, or cyclopropyl optionally substituted by methyl; and the 5(3)-substituent is S(CH.sub.2).sub.n OR.sup.2 where R.sup.2 is (C.sub.1 -C.sub.3)alkyl and n is 1 or 2.
The present invention discloses 1-dimethylcarbamoyl-3-substituted-5-substituted-1H-1,2,4-triazoles. These compounds are distinguished primarily by their novel 5-position substituents.
The 5-position acid and ester compounds of the present invention are distinguished by their excellent insecticidal activity against sucking insects of the order Homoptera and especially those of the family Aphididae. These acid and ester compounds are highly selective against aphids, possess very good contact action and are plant systemic through both foliar and root absorption; and exhibit very good residual properties as foliar deposits and through both foliar and root absorption and transport.
Certain compounds of the present invention, generally the 5-position carbonyl, amido, sulfonyl and sulfonamide compounds, exhibit a broader spectrum of activity against foliage feeding insects, such as those from the order Coleoptera, and Acarids, in addition to exhibiting activity against insects from the order Homoptera.
Certain compounds of the present invention are also distinguished by their plant growth regulator effect. Further, certain compounds of the present invention are distinguished by their molluscicidal activity.
Accordingly, compounds of the present invention are particularly suitable for controlling plant-destructive insects and/or acarids in crops of cultivated plants and ornamentals, especially in crops of fruits, vegetables and cereals. Certain compounds are suitable as plant growth regulating agents and certain compounds are suitable for controlling molluscs.
It is therefore an object of the present invention to provide novel compounds and compositions containing said compounds which possess selective aphpicidal activity. It is also an object of the present invention to provide novel compounds, and compositions containing said compounds which possess insecticidal and acaricidal activity. It is a further object of this invention to provide methods for controlling insects, acarids, regulating plant growth and/or controlling molluscs using the novel compounds.